Synthesis of Substituted 1,6-Diarylnaphthalenes via a Tandem Claisen Rearrangement and Ene Reaction Protocol

In this work, we developed a concise synthetic route for the synthesis of polysubstituted naphthalenes starting from commercially available isovanillin and its derivatives. Reaction with styryl bromide via O-styrylation, Claisen rearrangement, ene reaction, and O-alkylation occurred in high yields....

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Veröffentlicht in:Journal of organic chemistry 2017-03, Vol.82 (6), p.3317-3326
Hauptverfasser: Chan, Chieh-Kai, Chen, Yu-Hsin, Tsai, Yu-Lin, Chang, Meng-Yang
Format: Artikel
Sprache:eng
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Zusammenfassung:In this work, we developed a concise synthetic route for the synthesis of polysubstituted naphthalenes starting from commercially available isovanillin and its derivatives. Reaction with styryl bromide via O-styrylation, Claisen rearrangement, ene reaction, and O-alkylation occurred in high yields. The key structures were confirmed by single-crystal X-ray diffraction.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00108